Huperzine A and analogs thereof

The present invention relates to a method for the synthesis of certain bridged fused ring pyridines. Such bridged fused ring pyridines can be converted to huperzine A and analogs of huperzine A. The present invention also covers such bridged fused ring pyridines, compounds utilized for the preparation of the bridged fused ring pyridines and analogs of huperzine A.

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Claims

1. A compound having the general formula II: ##STR12## wherein: R.sub.1.sup.1 is selected from the group consisting of H and C.sub.1 -C.sub.8 linear or branched alkoxy;

R.sub.1.sup.2 is C.sub.1 -C.sub.8 linear or branched alkyl; and
n.sub.1 is an integer from 0 to 4.

2. The compound according to claim 1 wherein R.sub.1.sup.1 is a C.sub.1 -C.sub.8 linear or branched alkoxy.

3. The compound according to claim 2 wherein:

R.sub.1.sup.1 is OCH.sub.3;
R.sub.1.sup.2 is CH.sub.3; and
n.sub.1 is 1.
Referenced Cited
Other references
  • Kempter, G. et al., "Heterocycles from amino ketones. XX. Synthesis of quinolines, 1-aminonortricyclene and -quadricyclene derivatives", J. Prakt. Chem. 314(3-4), 543-556, 1972, see abstract, 1972. C. M. Yu et al., Canadian Journal of Chemistry, 64, 837-839 (1986), The Structures of Huperzine A and B, Two New Alkaloids Exhibiting Marked Anticholinesterase Activity. D. Gravel et al., Canadian Journal of Chemistry, 62, 2945-2947 (1984). Total Regiospecific Synthesis of Selagine Tricyclic Ring System. W. Ye et al., Acta Pharmacologica Sinica, 9, 193-196 (1988), Pharmacokinetics of Huperzine A in Rats and Mice. C. Shi-Ming et al., Acta Pharmaceutica Sinica, 22, 801-806 (1977), The Effects of Fordine on Learning and Memory in Rats. A. Kende et al., Heterocycles, 21, 91-106, New Tactics in Heterocyclic Synthesis, 1984. Valenta, Z. et al., "Structure of Selagine", CA 54:21167-21168 of Tetrahedron Letters, 1960, No. 10, pp. 26-33. Chen, C. et al., "Studies on the Bioactive Lyc. Alkaloid", CA 101:143940w of Tai-wan Yao Hsueh Toa Chih, 1984, vol. 36, #1, pp. 1-7. Liu(I), "Structure of Huperzine A and B", CA 105:75908x of Can. J. Chem., 1986, vol. 64, #4, pp. 837-839. Liu(II), "Chemistry of Huperzine A and B", CA 107:115821p of Huaxue Xueboo, 1986, vol. 44, #10, pp. 1035-1040. Yuan, S., et al., "Alkaloids of Huperzia Serrata", CA 110:92014y of Yaoxue Xuebao, 1988, vol. 23, No. 7, pp. 516-520. Qian, L. et al., "A Total Synthesis of (.+-.) Huperzine A", CA 111:214783s of Tetrahedron Letters, 1989, vol. 30, No. 16, pp. 2089-2090. Tang CA 106:12878n of Zhongguo Yaoli Xuebao 1986, 7(6)507-11. Chen II CA 108:143270x of Yauxue Xuebao 1987, 22(11), 801-6. Nyembo, CA 86:90108u of Bull. Chim. Belg. 1976 85(8), 595-604.
Patent History
Patent number: 5869672
Type: Grant
Filed: Jun 6, 1997
Date of Patent: Feb 9, 1999
Assignee: Mayo Foundation for Medical Education and Research (Rochester, MN)
Inventors: Alan Paul Kozikowski (Pittsburgh, PA), Yan Xia (Baltimore, MD)
Primary Examiner: Marianne M. Cintins
Assistant Examiner: Dwayne C. Jones
Law Firm: Pennie & Edmonds LLP
Application Number: 8/870,281